Young Spaniard Sergio Garcia carded an opening-round 66 to take the lead in the 1999 PGA Championship. At the age of 19, he battled 23-year-old Tiger Woods to the wire, but in the end the savvy Woods came out ahead with an epic Sunday matchup. The 81st PGA Championship was played at Medinah Country Club in Medinah, Ill. right outside of Chicago. Woods won by one shot in a matchup that many predicted would turn into a rivalry for years to come. It marked Woods' second career major championship and first PGA title. It would take 18 years for Garcia to win his first major when he broke through with a win at the Masters in 2017. Woods has autographed this limited edition (500) 1999 PGA Championship pin flag in black paint pen. His signature is deemed authentic by virtue of Upper Deck Authenticated's Five-Step Process.